


Cherry Bomb

by castielshoneybee



Series: Carry On Wayward Son [5]
Category: Supernatural
Genre: Dean and Reader have a history, F/M, First Time, Smut
Language: English
Status: Completed
Published: 2016-08-31
Updated: 2016-08-31
Packaged: 2018-08-12 06:03:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,111
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7923364
Author URL: https://archiveofourown.org/users/castielshoneybee/pseuds/castielshoneybee
Summary: <blockquote class="userstuff">
              <p>Dean and the reader took one another's virginity as teenagers. Years later, they meet again on a hunt.</p>
            </blockquote>





	Cherry Bomb

**Author's Note:**

> Inspired by The Runaways

_Hey street boy, what's your style_  
_Your dead end dreams don't make you smile_  
_I'll give ya something to live for_  
_Have ya, grab ya til you're sore..._

April 14, 2006, Fort Dodge, Iowa

Probably a werewolf, you think, pulling up to the scene. You get out of the car, adjusting your skirt as you straighten up. You walk purposefully up to the uniformed officer standing behind the crime scene tape and flash your badge.

"Right this way, Agent Currie. Your colleagues are already here." Colleagues? Shit. Talking your way out of this one isn't going to be fun. He leads you toward two men in suits. One of them turns slightly, and you catch his profile. Relief mingles with annoyance. Dean Winchester. You sigh mentally. At least you weren't dealing with real feds, though in all honesty, that might have been easier. "Agent Osbourne, Agent Rhoads?" the officer says. They turn toward you. Dean isn't quite able to hide his surprise. The officer returns to his post.

"Well, well. Dean Winchester." Your voice doesn't betray the pounding in your chest. If it's possible, he's even more handsome than he was at sixteen. He's filled out, but he still has that adorable smattering of freckles, and his eyes are the same jade green. You turn to the other man. "Sam? Is that you? My god, you've had a growth spurt or five since the last time I saw you!" Sam smiles at you. Dean just stands there looking stunned.

"Oh, man! It's so good to see you!" Sam's joy at seeing you makes up for the fact that Dean hasn't said a word. "I'd hug you, but the bureau probably doesn't approve of their agents hugging on the job." He grins, and you laugh, lightly touching his arm. Dean finally snaps out of it, remembering what he's supposed to be doing.

"Hey. It's been a long time."

"Yeah, it has." You look at one another for a moment. "So, tell me about the case. I don't usually play well with others, but since we're all here, we might as well work together."

"I don't know..." Dean looks at the ground and kicks the dirt at his feet.

"Come on, Dean, another pair of hands will just help us wrap this up faster." At least Sam has your back.

"Fine," he says reluctantly. They fill you in. Two victims, hearts removed. Pretty obviously a werewolf. You finish at the scene and head to the ME's to check out the bodies. What you see confirms your suspicions. You head back to the motel where it turns out you're all staying. That's not such a surprise considering the lack of accommodations in the area. You head to your room to change out of your suit, promising to meet up with Sam and Dean in their room to figure out where the werewolf is. As you drop your bag on the chair, you reminisce.

****

July 25, 1995, Sioux Falls, South Dakota

You hate staying at Bobby's. You tried to convince your mom to let you go on the hunt with her. It was just a couple of ghouls, but she insisted on leaving you. It's so boring here! You sit on the porch, avoiding Bobby, who clucks around you like a mother hen. A car pulls into the salvage yard, dust flying from its tires. 67 Impala. Nice. A man, a boy around your age, and a younger boy all pile out, grabbing bags from the trunk. The man addresses you as they approach the porch.

"Bobby around?" You eye him suspiciously. Obviously a hunter, but you've never met him before.

"Depends. Who are you?"

"John Winchester. Can you tell him we're here?" You push yourself up with a sigh and head inside.

"Hey, Bobby! Some guy named John Winchester's here!" you yell through the house.

"Well, tell him to come in, cupcake." You hate when he calls you that. You poke your head out the door.

"C'mon in." They file into the house. The younger boy sprints past everyone, throwing himself into Bobby's arms. John shakes Bobby's hand, and the two walk away, already deep in conversation. The older boy stops next to you.

"I'm Dean." You introduce yourself, checking him out. He's cute in sort of a bad boy way. Leather jacket, dirty blonde hair. The freckles are cute. His eyes are beautiful. "So, are you staying here?"

"Yeah, my mom's on a hunt and wouldn't let me go with her. I'm gonna be sixteen in two weeks. I think I can handle a couple of ghouls, but no. 'It's too dangerous.' I have to stay at Bobby's." You roll your eyes. He smiles in sympathy.

"I hear ya. We're here for the same reason. Dad thinks a nest of vamps is too much for me to handle." His eye roll mirrors yours, and you both laugh.

****

August 8, 1995

Sweet sixteen. Bobby has a cake for you and a gift your mom left. It's a journal. All hunters keep one. You smile. Maybe she'll start treating you like one now. At least Dean gets you. He sees you as a woman, a hunter. After your little party, you and Dean take a walk through the yard, holding hands. It didn't take long for the two of you to get hot and heavy. You spend most of your time making out wherever you can manage to hide from Sam. You climb into the back of a rusted out Chevy. It's one of your favorite spots. You've decided that tonight's gonna be the night. Dean climbs in after you and muscles the door shut. He dives on top of you, and you giggle. He kisses you, and your tongues duel. He reaches up and palms your breast through your T-shirt. You cross your arms at the hem and pull it over your head. He leans in and plants kisses along the tops of your breasts, reaching for the clasp of your bra. He fumbles with it, so you reach back and help him. This is it. The furthest you've ever gone with a boy. He sucks in a breath at the sight of your bare breasts, then takes one nipple hesitantly into his mouth. You gasp. You can feel his erection through both your jeans and move against it a little. He moans and starts to unbutton your jeans. You put a hand on his to stop him.

"Dean, I have to tell you something. I... I've never done it before." You hope he doesn't reject you.

"You haven't?" He sighs in relief. "I'll be honest. Neither have I." You both break out in nervous giggles. With the tension broken, you both quickly unbutton your jeans and pull them off. You look at one another, not believing this is really happening.

"You sure?" He asks. You nod. "You ready?" You nod again. You both pull your underwear off and look at each other. Are they all that big? You don't have time to think of anything else as you both start grabbing at one another. Mouths and hands fly across skin.

"Do you have a condom?" You push your hand against his chest.

"Oh, yeah. I've been carrying it in my pocket for a week now, just in case." You giggle again as he fumbles it on. He enters you slowly. It's okay at first, but when he gets all the way in, it hurts. You'd heard it would. Then, just when it starts to kinda feel good, it's over. That's it? Man, sex is overrated. You hope it gets better. Still, you're glad your first time was with Dean. He's special.

****

April 14, 2006

And that was it. The next morning, you awoke to find that John had picked them up before dawn, and they were on the road. You didn't even get to say goodbye. You've asked Bobby about him over the years, but you've never run into him until now.

You shake yourself out of your reverie and finish changing your clothes, then head over to their room.

****

April 15, 2006

The hunt had been easy. Once you figured out where the werewolf was holed up, you waited for him and took him out fast. Things were kind of awkward. Sam did most of the talking. You caught Dean sneaking glances at you, then looking away guiltily when he realized you'd caught him. He hardly said anything to you, and nothing that wasn't related to the hunt. You all headed back to the motel, intending to leave in the morning. Sitting in your room, you can't stop thinking about Dean. You wonder how his skills have improved since your fumbles in the back of the Chevy. You imagine his strong hands running over your skin. There's a knock at the door. You open it, and there he stands.

"Can I come in?" You motion him inside. He sits awkwardly at the end of your bed, looking down at his boots. You sit down next to him.

"Look, I..." "Hey, I'm..." You both laugh as you start talking at the same time.

"Me first, okay?" he says. " I'm sorry. I'm sorry I left like I did. I wanted to wake you up to say goodbye, but my dad is a major hardass, and he barely gave me enough time to pack my stuff."

"I know. I don't blame you. It hurt a little, I'm not gonna lie, but it's the hunter's life, especially for hunters' kids." You give him a small smile.

"I ask Bobby about you sometimes," he confesses.

"You do? Me too. Dean, I'm still glad my first time was with you, even though it sucked."

"I thought it was awesome!" He gives you a cocky grin.

"For you, maybe! Neither one of us knew what the hell we were doing." You smile. "But you know what?" You scoot closer. "I'll bet we've both improved since then." He looks at you for a beat, then leans over and kisses you. You reach your arms around his neck and pull him closer, parting your lips to allow his tongue entry. His kiss is comforting. You delve into one another's mouths, enjoying the familiarity even after all this time. He slides his hands under your shirt, bringing it up over your head, then reaches up your back to unclasp your bra with a flick. No fumbles this time. His mouth moves from yours to devour your breasts, sucking and nipping each nipple in turn. You arch against him, pleasure building in your core. You grab his shirt and tug at it, and he leaves your breasts to help you get it over his head. You both fall back on the bed, hands roaming over one another, lips kissing and licking, never stopping. Your hands reach down and unbuckle his belt. He drops to his back, kicks off his boots, unbuttons his jeans, and pulls them down, lifting his hips off the bed to help them off, bringing his boxers along with them. You follow suit. You look him up and down, eyes stopping at his erection. If there's one thing you've learned over the years, it's that they're definitely not all that big. You take him in your hand and slowly start pumping him. His head falls back against the bed with a groan.

"Hold that thought." He whimpers as your hand leaves him. You dash as quickly as you can to your purse and retrieve the condom you keep there. Back in a flash, you expertly roll it on, then straddle him, positioning yourself over him. You sink onto him, and it feels like coming home. You begin riding him, rolling your hips as he thrusts his upward. You take it slow, pleasure building until it's driving you both crazy. Finally, it's too much. He flips you onto your back, never leaving you, and begins to thrust faster. You moan, edging closer and closer to your orgasm as he hits your g-spot with every thrust. He reached his hand down and begins rubbing circles on your clit with his thumb, and you come undone, walls spasming around him. His thrusts become erratic, and he follows you over his peak. You lie in a tangled heap for what seems like forever, just feeling one another breathe. Dean breaks the silence.

"So, yeah, _that_ was awesome." You smile and give him a peck on the cheek.

"Definitely a huge improvement. Maybe we don't wait another eleven years before doing it again?"

"Let me check my calendar. Hmm, looks like I'm free for forever." You laugh as he dives on top of you again.


End file.
